ArticleJournal of the American Chemical Society2018
Copper-Catalyzed Vinylogous Aerobic Oxidation of Unsaturated Compounds with Air.
Article in Journal of the American Chemical Society, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed.
- Mild Direct Remote Hydroxylation of Enals in Air.The Journal of organic chemistry · 2026Article
- Outcompeting hydrofunctionalization: Asymmetric remote substitution of alkynes.Science advances · 2025Article
- P(V)-Promoted Rh-Catalyzed Highly Regioselective Hydroformylation of Styrenes under Mild Conditions.Molecules (Basel, Switzerland) · 2024Article
- Facile synthesis of newRSC advances · 2023Article
- A Convergent Total Synthesis of (+)-Ineleganolide.Journal of the American Chemical Society · 2023Article
- Chemoselektive γ-Oxidation von β,γ-ungesättigten Amiden mit TEMPO.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2021Article
- Chemoselective γ-Oxidation of β,γ-Unsaturated Amides with TEMPO.Angewandte Chemie (International ed. in English) · 2021Article
- Computational exploration of copper catalyzed vinylogous aerobic oxidation of unsaturated compounds.Scientific reports · 2021Article
- New Developments of the Principle of Vinylogy as Applied to π-Extended Enolate-Type Donor Systems.Chemical reviews · 2020Article
- Synthesis of γ-substituted carbonyl compounds from DMSO-mediated oxidation of enynamides: mechanistic insights and carbon- and hetero-functionalizations.Chemical science · 2019Article
- Acid-Catalyzed Air-Oxidative Fragmentation of the Carbon-Carbon Bond in 2-Aryl-1-tetralones.ACS omega · 2019Article
- Copper-Promoted Functionalization of Organic Molecules: from Biologically Relevant Cu/OChemical reviews · 2019Review
Corrections and comments
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Authors and funding
7 authors.
Funding
Abstract
A mild and operationally simple copper-catalyzed vinylogous aerobic oxidation of β,γ- and α,β-unsaturated esters is described. This method features good yields, broad substrate scope, excellent chemo- and regioselectivity, and good functional group tolerance. This method is additionally capable of oxidizing β,γ- and α,β-unsaturated aldehydes, ketones, amides, nitriles, and sulfones. Furthermore, the present catalytic system is suitable for bisvinylogous and trisvinylogous oxidation. Tetramethylguanidine (TMG) was found to be crucial in its role as a base, but we also speculate that it serves as a ligand to copper(II) triflate to produce the active copper(II) catalyst. Mechanistic experiments conducted suggest a plausible reaction pathway via an allylcopper(II) species. Finally, the breadth of scope and power of this methodology are demonstrated through its application to complex natural product substrates.
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